US5091468A - Organosilane coating composition - Google Patents
Organosilane coating composition Download PDFInfo
- Publication number
- US5091468A US5091468A US07/471,349 US47134990A US5091468A US 5091468 A US5091468 A US 5091468A US 47134990 A US47134990 A US 47134990A US 5091468 A US5091468 A US 5091468A
- Authority
- US
- United States
- Prior art keywords
- coating composition
- epoxycyclohexyl
- glycidoxypropyl
- organosilane compound
- antistatic coating
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000008199 coating composition Substances 0.000 title claims abstract description 46
- 150000001282 organosilanes Chemical class 0.000 title description 3
- -1 organosilane compound Chemical class 0.000 claims abstract description 46
- 239000011248 coating agent Substances 0.000 claims abstract description 18
- 238000000576 coating method Methods 0.000 claims abstract description 18
- RGPUVZXXZFNFBF-UHFFFAOYSA-K diphosphonooxyalumanyl dihydrogen phosphate Chemical compound [Al+3].OP(O)([O-])=O.OP(O)([O-])=O.OP(O)([O-])=O RGPUVZXXZFNFBF-UHFFFAOYSA-K 0.000 claims abstract description 16
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims description 20
- 230000007062 hydrolysis Effects 0.000 claims description 18
- 238000006460 hydrolysis reaction Methods 0.000 claims description 18
- 238000006068 polycondensation reaction Methods 0.000 claims description 15
- 239000002798 polar solvent Substances 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000012454 non-polar solvent Substances 0.000 claims description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 claims description 3
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 claims description 3
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 claims description 3
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 claims description 3
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 claims description 3
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 claims description 3
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 claims description 3
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 claims description 3
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 claims description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 claims description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 229940072049 amyl acetate Drugs 0.000 claims description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 2
- ZZNQQQWFKKTOSD-UHFFFAOYSA-N diethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OCC)(OCC)C1=CC=CC=C1 ZZNQQQWFKKTOSD-UHFFFAOYSA-N 0.000 claims description 2
- MNFGEHQPOWJJBH-UHFFFAOYSA-N diethoxy-methyl-phenylsilane Chemical compound CCO[Si](C)(OCC)C1=CC=CC=C1 MNFGEHQPOWJJBH-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims description 2
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- ASGKDLGXPOIMTM-UHFFFAOYSA-N diethoxy-methyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](C)(OCC)OCC)CCC2OC21 ASGKDLGXPOIMTM-UHFFFAOYSA-N 0.000 claims 2
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 claims 2
- SLQTWNAJXFHMHM-UHFFFAOYSA-N dimethoxy-methyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](C)(OC)OC)CCC2OC21 SLQTWNAJXFHMHM-UHFFFAOYSA-N 0.000 claims 2
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 claims 2
- HHBOIIOOTUCYQD-UHFFFAOYSA-N ethoxy-dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(C)CCCOCC1CO1 HHBOIIOOTUCYQD-UHFFFAOYSA-N 0.000 claims 2
- YKSZBBZEHPPESP-UHFFFAOYSA-N methoxy-dimethyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](C)(C)OC)CCC2OC21 YKSZBBZEHPPESP-UHFFFAOYSA-N 0.000 claims 2
- FBNXYLDLGARYKQ-UHFFFAOYSA-N methoxy-dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(C)CCCOCC1CO1 FBNXYLDLGARYKQ-UHFFFAOYSA-N 0.000 claims 2
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 claims 2
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 claims 2
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 claims 2
- WHBCLAYELHHRNR-UHFFFAOYSA-N ethoxy-dimethyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](C)(C)OCC)CCC2OC21 WHBCLAYELHHRNR-UHFFFAOYSA-N 0.000 claims 1
- FKDLBUPSJQZYFZ-UHFFFAOYSA-N ethoxy-ethyl-dimethylsilane Chemical compound CCO[Si](C)(C)CC FKDLBUPSJQZYFZ-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 239000011147 inorganic material Substances 0.000 abstract description 2
- 239000007769 metal material Substances 0.000 abstract description 2
- 239000011368 organic material Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- LBDROUOCQSGOFI-UHFFFAOYSA-N methanol;phosphoric acid Chemical compound OC.OP(O)(O)=O LBDROUOCQSGOFI-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S524/91—Antistatic compositions
- Y10S524/912—Contains metal, boron, phosphorus, or silicon
Abstract
Description
CH.sub.3 Si(OR).sub.3 ;
______________________________________ Methyltrimethoxysilane 25 g γ-Glycidoxypropyltrimethoxysilane 25 g 50 wt % Aqueous Solution of Aluminum 10 g Dihydrogenphosphate Methanol 50 g ______________________________________
______________________________________ Condition for Curing Pencil Hardness ______________________________________ 25° C., 1 hr. 3H 25° C., 24 hrs. 6H 70° C., 2 hrs. 5H 100° C., 2 hrs. 9H ______________________________________
______________________________________ Normal Condition (25° C., 55% RH*) 1.0 sec. 25° C., 30% RH* 5.0 sec. After being treated at 70° for 100 hrs. 11.9 sec. ______________________________________ *Note: RH = Relative Humidity
Claims (11)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1169793A JPH0335073A (en) | 1989-07-03 | 1989-07-03 | Production of inorganic coating composition |
JP1-169793 | 1989-07-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
US5091468A true US5091468A (en) | 1992-02-25 |
Family
ID=15892989
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/471,349 Expired - Fee Related US5091468A (en) | 1989-07-03 | 1990-01-29 | Organosilane coating composition |
Country Status (3)
Country | Link |
---|---|
US (1) | US5091468A (en) |
JP (1) | JPH0335073A (en) |
CA (1) | CA2010969C (en) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0585886A1 (en) * | 1992-08-31 | 1994-03-09 | Matsushita Electric Industrial Co., Ltd. | Antistatic film and method of manufacturing the same |
WO1995000259A2 (en) * | 1993-06-21 | 1995-01-05 | Elf Atochem North America, Inc. | Brittle oxide substrates strengthened by cross-linkable silanes |
US5567235A (en) * | 1990-08-30 | 1996-10-22 | Elf Atochem North America, Inc. | Method for strengthening a brittle oxide substrate, silane-based compositions, and a polymerized cross-linked siloxane coated brittle oxide substrate |
US5728203A (en) * | 1995-10-26 | 1998-03-17 | Lord Corporation | Aqueous protective and adhesion promoting composition |
WO1998022548A1 (en) * | 1996-11-22 | 1998-05-28 | Philips Electronics N.V. | Lacquer composition |
EP0845489A2 (en) * | 1996-11-27 | 1998-06-03 | Fraunhofer-Gesellschaft Zur Förderung Der Angewandten Forschung E.V. | Antistatic agent, process for its preparation and its use in the production of antistatic coatings |
US6013333A (en) * | 1990-08-30 | 2000-01-11 | Elf Atochem North America, Inc. | Method for strengthening a brittle oxide substrate |
US6037008A (en) * | 1998-09-08 | 2000-03-14 | Ck Witco Corporation | Use of emulsified silane coupling agents as primers to improve adhesion of sealants, adhesives and coatings |
WO2001032789A1 (en) * | 1999-11-01 | 2001-05-10 | 3M Innovative Properties Company | Curable inkjet printable ink compositions |
US6793971B2 (en) | 2001-12-03 | 2004-09-21 | Cardinal Ig Company | Methods and devices for manufacturing insulating glass units |
US6955832B2 (en) | 2001-03-16 | 2005-10-18 | Novartis Ag | Colored printing ink for contact lenses |
US20060023044A1 (en) * | 2004-07-29 | 2006-02-02 | Bauer Richard D | Fixing fluid and inkjet ink sets comprising same |
DE102005001616A1 (en) * | 2005-01-12 | 2006-07-20 | Huhtamaki Forchheim Zweigniederlassung Der Huhtamaki Deutschland Gmbh & Co. Kg | Antistatic surface finish |
US20090264316A1 (en) * | 2008-04-17 | 2009-10-22 | Marshall University Research Corporation | Ultraviolet/Ozone Patterned Organosilane Surfaces |
CN115260899A (en) * | 2022-07-28 | 2022-11-01 | 广东美的白色家电技术创新中心有限公司 | Hydrophobic coating and preparation method and application thereof |
CN116355525A (en) * | 2021-12-28 | 2023-06-30 | 九州高科技株式会社 | Inorganic glass coating agent |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100521889B1 (en) * | 2001-01-19 | 2005-10-17 | 바이오시스텍 주식회사 | Container having functions of removing ethylene and suppressing generation of ethylene |
JP4680611B2 (en) * | 2004-01-20 | 2011-05-11 | 株式会社砺波商店 | Tableware |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4354013A (en) * | 1980-01-22 | 1982-10-12 | Toshiba Silicone Co., Ltd. | Process for preparing epoxy-modified silicone resins |
US5008328A (en) * | 1985-08-21 | 1991-04-16 | Kansai Paint Co., Ltd. | Aqueous organosilicon resin coating compositions |
-
1989
- 1989-07-03 JP JP1169793A patent/JPH0335073A/en active Granted
-
1990
- 1990-01-29 US US07/471,349 patent/US5091468A/en not_active Expired - Fee Related
- 1990-02-27 CA CA002010969A patent/CA2010969C/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4354013A (en) * | 1980-01-22 | 1982-10-12 | Toshiba Silicone Co., Ltd. | Process for preparing epoxy-modified silicone resins |
US5008328A (en) * | 1985-08-21 | 1991-04-16 | Kansai Paint Co., Ltd. | Aqueous organosilicon resin coating compositions |
Cited By (25)
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US5567235A (en) * | 1990-08-30 | 1996-10-22 | Elf Atochem North America, Inc. | Method for strengthening a brittle oxide substrate, silane-based compositions, and a polymerized cross-linked siloxane coated brittle oxide substrate |
US6013333A (en) * | 1990-08-30 | 2000-01-11 | Elf Atochem North America, Inc. | Method for strengthening a brittle oxide substrate |
EP0585886A1 (en) * | 1992-08-31 | 1994-03-09 | Matsushita Electric Industrial Co., Ltd. | Antistatic film and method of manufacturing the same |
US5449554A (en) * | 1992-08-31 | 1995-09-12 | Matsushita Electric Industrial Co., Ltd. | Antistatic film and method of manufacturing the same |
WO1995000259A2 (en) * | 1993-06-21 | 1995-01-05 | Elf Atochem North America, Inc. | Brittle oxide substrates strengthened by cross-linkable silanes |
WO1995000259A3 (en) * | 1993-06-21 | 1995-02-09 | Atochem North America Elf | Brittle oxide substrates strengthened by cross-linkable silanes |
US5728203A (en) * | 1995-10-26 | 1998-03-17 | Lord Corporation | Aqueous protective and adhesion promoting composition |
US5902645A (en) * | 1995-10-26 | 1999-05-11 | Lord Corporation | Aqueous protective and adhesion promoting composition |
WO1998022548A1 (en) * | 1996-11-22 | 1998-05-28 | Philips Electronics N.V. | Lacquer composition |
EP0845489A2 (en) * | 1996-11-27 | 1998-06-03 | Fraunhofer-Gesellschaft Zur Förderung Der Angewandten Forschung E.V. | Antistatic agent, process for its preparation and its use in the production of antistatic coatings |
EP0845489A3 (en) * | 1996-11-27 | 1998-08-19 | Fraunhofer-Gesellschaft Zur Förderung Der Angewandten Forschung E.V. | Antistatic agent, process for its preparation and its use in the production of antistatic coatings |
US6037008A (en) * | 1998-09-08 | 2000-03-14 | Ck Witco Corporation | Use of emulsified silane coupling agents as primers to improve adhesion of sealants, adhesives and coatings |
WO2001032789A1 (en) * | 1999-11-01 | 2001-05-10 | 3M Innovative Properties Company | Curable inkjet printable ink compositions |
US6461419B1 (en) | 1999-11-01 | 2002-10-08 | 3M Innovative Properties Company | Curable inkjet printable ink compositions |
US6582804B2 (en) * | 1999-11-01 | 2003-06-24 | 3M Innovative Properties Company | Curable inkjet printable ink compositions |
US6719422B2 (en) * | 1999-11-01 | 2004-04-13 | 3M Innovative Properties Company | Curable inkjet printable ink compositions |
US6955832B2 (en) | 2001-03-16 | 2005-10-18 | Novartis Ag | Colored printing ink for contact lenses |
US6793971B2 (en) | 2001-12-03 | 2004-09-21 | Cardinal Ig Company | Methods and devices for manufacturing insulating glass units |
US20050013950A1 (en) * | 2001-12-03 | 2005-01-20 | Cardinal Ig Company | Methods and devices for manufacturing insulating glass units |
US20060023044A1 (en) * | 2004-07-29 | 2006-02-02 | Bauer Richard D | Fixing fluid and inkjet ink sets comprising same |
US7530683B2 (en) * | 2004-07-29 | 2009-05-12 | E.I. Du Pont De Nemours And Company | Fixing fluid and inkjet ink sets comprising same |
DE102005001616A1 (en) * | 2005-01-12 | 2006-07-20 | Huhtamaki Forchheim Zweigniederlassung Der Huhtamaki Deutschland Gmbh & Co. Kg | Antistatic surface finish |
US20090264316A1 (en) * | 2008-04-17 | 2009-10-22 | Marshall University Research Corporation | Ultraviolet/Ozone Patterned Organosilane Surfaces |
CN116355525A (en) * | 2021-12-28 | 2023-06-30 | 九州高科技株式会社 | Inorganic glass coating agent |
CN115260899A (en) * | 2022-07-28 | 2022-11-01 | 广东美的白色家电技术创新中心有限公司 | Hydrophobic coating and preparation method and application thereof |
Also Published As
Publication number | Publication date |
---|---|
CA2010969C (en) | 1999-05-11 |
CA2010969A1 (en) | 1991-01-03 |
JPH0545612B2 (en) | 1993-07-09 |
JPH0335073A (en) | 1991-02-15 |
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